Reaction of diimines and benzyne

Phenylbiguanide as electron donor in heterocyclic synthesis

“…Our long-term interest in chemical reactions induced by charge-transfer complexation forms a part of our systematic efforts to obtain new heterocyclic systems [18][19][20][21][22][23][24][25][26][27]. We have turned our attention to phenylbiguanide as electron donor towards some -acceptors, such as tetracynoethylene (TCNE), 2-dicyanomethyleneindane-1,3-dione (CNIND), 2,3-dicyano-1,4-naphthoquinone (DCNQ), tetracyanoquinodimethane (TCNQ), and 3,4,5,6-tetrachloro-1,2-benzoquinone (CHL-o), to synthesize some heterocycles with the expectation that they too might exhibit biological activity.…”

4.09 Nucleophilic Coupling with Arynes

“…The resulting benzoazetines are susceptible to valence isomerization into aza-ortho-xylylenes (94), which furnish acridine derivatives by electrocyclization and aromatization (Scheme 80). 240,241 A similar reaction using oxazolones leads to the formation of benzoxazepine derivatives, 242 being attributable to addition of water to the aza-ortho-xylylene intermediates (Scheme 81). The [2 þ 2] cycloaddition with aldehydes smoothly proceeds to afford benzoxete 95 in a similar manner as above.…”

Synthesis and Spectral Analysis of 3,4,5‐trichloro‐6‐(dibenzo[d,f][1,3]diazepin‐5‐yl)‐[1,2]‐benzoquinones

“…Alternatively this quinone may undergo nucleophilic attack by e.g. the N-atoms of N,N'-dibenzylidene ethylenediamine at both carbonyl groups and at the chlorine atoms followed by condensation (elimination of either H 2 O or HCl) 9 . Later we have synthesized various 4-aryl-5-imino-3-phenyl-1H-naphtho[2,3-f ]-1,2,4-triazepine-6,11-diones via reaction of amidrazones with 1,4-dioxo-1, 4-dihydronaphthalene-2,3-dicarbonitrile 10 .…”